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6-Chloro-1,3-dihydroindol-2-one → Z-3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentylidene]-6-chloro-1,3-dihydro-indol-2-one

HRID 2065415
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2065415
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[C:12]([Si:16]([CH3:27])([CH3:26])[O:17][CH2:18][CH2:19][C:20]([CH3:25])([CH3:24])[CH2:21][CH:22]=O)([CH3:15])([CH3:14])[CH3:13].C[O-].[Na+]>CO>[C:12]([Si:16]([CH3:26])([CH3:27])[O:17][CH2:18][CH2:19][C:20]([CH3:25])([CH3:24])[CH2:21]/[CH:22]=[C:6]1\[C:7](=[O:11])[NH:8][C:9]2[C:5]\1=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)([CH3:15])([CH3:14])[CH3:13]
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Komponenten

5

Edukt 3

HCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 10942334Sodium MethoxideHCID 219327085-(Tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentanal

Produkt 1

HCID 86656671Z-3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentylidene]-6-chloro-1,3-dihydro-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887Methanol
Lösungsmittel

Versuchsvorschrift

To the mixture of 6-chlorooxindole (3.3 g, 20 mmol) (Crescent) and 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentanal (6.5 g, 26.6 mmol) in methanol (150 mL) was added a methanolic solution (25%, Aldrich) of sodium methoxide (10 g, 46 mmol) dropwise. The reaction mixture was stirred at room temperature for 10 min. The solvent was removed, and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by chromatography (25-33% EtOAc in hexanes) to give E/Z-3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentylidene]-6-chloro-1,3-dihydro-indol-2-one as a off white solid (Yield 3.6 g, 46%).

Aufarbeitung

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (25-33% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2f5de777922e4ea7a85369aedbb6ecfd
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08288431B2

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